An efficient synthesis of synargentolide A from d-mannitol

An efficient synthesis of synargentolide A is described by using d-mannitol and d-malic acid. The key features of the synthetic strategy include Wittig olefination, ring closing-metathesis reaction and cross-metathesis reaction for the formation of synargentolide A.

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(4S,4′R,5R)-2,2,2′,2′-Tetramethyl-5-vinyl-4,4′-bi(1,3-dioxolane)C12H20O4[α]D26=-3.1 (c 1 CHCl3Source of chirality: d-mannitolAbsolute configuration: (4S,4′R,5R)

2-((4S,4′R,5R)-2,2,2′,2′-Tetramethyl-4,4′-bi(1,3-dioxolan)-5-yl)ethanolC12H22O5[α]D26=+10.2 (c 1 CHCl3)Source of chirality: d-mannitolAbsolute configuration: (4S,4′R,5R)

(4S,4′R,5R)-5-Allyl-2,2,2′,2′-tetramethyl-4,4′-bi(1,3-dioxolane)C13H22O4[α]D26=+4.3 (c 1 CHCl3)Source of chirality: d-mannitolAbsolute configuration: (4S,4′R,5R)

(R)-1-((4R,5R)-5-allyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diolC10H18O4[α]D26=+10.9 (c 1 CHCl3)Source of chirality: d-mannitolAbsolute configuration: (R)-1-((4R,5R)

(R)-1-((4R,5R)-5-Allyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethanolC10H18O3[α]D26=+5.2 (c 1 CHCl3)Source of chirality: d-mannitolAbsolute configuration: (R)-1-((4R,5R)

(2R,3R,4R)-Hept-6-ene-2,3,4-triolC7H14O3[α]D26=-10.3 (c 1 CHCl3)Source of chirality: d-mannitolAbsolute configuration: (2R,3R,4R)

(2R,3R,4R)-Hept-6-ene-2,3,4-triyl triacetateC13H20O6[α]D26=+23.8 (c 1 CHCl3)Source of chirality: d-mannitolAbsolute configuration: (2R,3R,4R)

(R)-1-((1-(2,2-Dimethyl-1,1-diphenylpropoxy)pent-4-en-2-yloxy)methyl)-4 methoxybenzeneC29H36O3Si[α]D26=+11.6 (c 1 CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (1R)

(R)-1-(2,2-Dimethyl-1,1-diphenylpropoxy)pent-4-en-2-olC21H28O2Si[α]D26=+4.2 (c 1 CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (1R)

(R)-1-(2,2-Dimethyl-1,1-diphenylpropoxy)pent-4-en-2-yl acrylateC24H30O3Si[α]D26=+8.3 (c 1 CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (1R)

(R)-6-((2,2-Dimethyl-1,1-diphenylpropoxy)methyl)-5,6-dihydropyran-2-oneC22H26O3Si[α]D26=+47.8 (c 1 CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (6R)

(R)-6-(Hydroxymethyl)-5,6-dihydropyran-2-oneC6H8O3[α]D26=+120.8 (c 1 CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (6R)

(R)-6-Vinyl-5,6-dihydropyran-2-oneC6H8O3[α]D26=+90.8 (c 1 CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (6R)

(1R,2R,4E)-2-(Acetyloxy)-1-[(1R)-1-(acetyloxy)ethyl]-5-[(2R)-6-oxo-3,6-dihydro-2H-2-pyranyl]-4-pentenyl acetate (synargentolide A)C18H24O8[α]D26=+36.5 (c 1 CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (1R,2R,4E), (1R), (2R)